Dichloromethane → (3beta)-3-[(1-Ethoxyethyl)oxy]pregn-5-en-20-one

HRID 1069049

Reaction equation

HRID 1069049 reaction equation
[OH:1][C@H:2]1[CH2:21][CH2:20][C@@:19]2([CH3:22])[C:4](=[CH:5][CH2:6][C@@H:7]3[C@@H:18]2[CH2:17][CH2:16][C@@:15]2([CH3:23])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C:12](=[O:14])[CH3:13])[CH2:3]1.C(N([CH2:29][CH3:30])CC)C.[C:31](=[O:34])([O-])O.[Na+].Cl[CH2:37]Cl>C(OCC)=C>[CH2:31]([O:34][CH:29]([O:1][C@H:2]1[CH2:21][CH2:20][C@@:19]2([CH3:22])[C:4](=[CH:5][CH2:6][C@@H:7]3[C@@H:18]2[CH2:17][CH2:16][C@@:15]2([CH3:23])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C:12](=[O:14])[CH3:13])[CH2:3]1)[CH3:30])[CH3:37]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 8955PregnenoloneHCID 516892Sodium Bicarbonate

Product 1

HCID 54547839(3beta)-3-[(1-Ethoxyethyl)oxy]pregn-5-en-20-one

Reagents, catalysts & solvents 1

HCID 8023Ethyl vinyl etherSolvent

Procedure

—Pyridium p-toluenesulfonate (6.32 g) was added to a solution of (3β)-3-hydroxypregn-5-en-20-one (1; 100 g) in dichloromethane (600 ml) and ethyl vinyl ether (200 ml). After stirring of the reaction mixture for 1 h at room temperature triethylamine (20 ml) was added, whereupon the mixture was poured into a saturated aqueous solution of sodium hydrogen carbonate (1 l). The product was extracted into dichloromethane; the combined organic phases were washed with brine, dried over sodium sulfate, and concentrated under reduced pressure to give (3β)-3-[(1-ethoxyethyl)oxy]pregn-5-en-20-one (2; 125.6 g), which was used in the following step without further purification.

Workup

  1. additionwas added, whereupon the mixture
  2. extractionThe product was extracted into dichloromethane
  3. washthe combined organic phases were washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-961e77002bc44415953e0afe8929298c
Source dataset
uspto-grants-2001_06
Patent number
US06251887B1

Linked notes

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